Synthesis of dioxazaborocines from N-substituted-bis(2-hydroxyaryl)aminomethylamines

Woodgate, Paul D.; Horner, Gillian; Maynard, N.Paul; Rickard, Clifton E. F.

doi:10.1016/s0022-328x(99)00510-0

Cited by 15 publications

(5 citation statements)

References 14 publications

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“…The Mannich reaction affects the aminomethylation of carbonyl and activated aromatic compounds 6,7 and accommodates a range of amines including amino alcohols, N-benzylamino alcohols, 8,9 N,N-dibenzylamino alcohols, [10][11][12] 3,4-dihydro-2H-1,3-benzoxazines, [13][14][15] (1,3-oxazolidin-3-yl)methylphenols and (1,3-morpholin-3-yl)methyl phenols. 15,16 Despite this precedent and our understanding of the Mannich reaction, we could not predict the outcome and preference for tautomeric forms in Mannich reactions using isoflavones and various ω-amino-1-alcohols.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

et al. 2015

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The aminomethylation of hydroxylated isoflavones with 2-aminoethanol, 3-amino-1-propanol, 4-amino-1-butanol, and 5-amino-1-pentanol in the presence of excess formaldehyde led principally to 9-(2-hydroalkyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]-oxazin-4-ones 4 and/or the tautomeric 7-hydroxy-8-(1,3-oxazepan-3-ylmethyl)-4H-chromen-4-ones 5. The ratio of these tautomers was dependent on solvent polarity, electronic effects of aryl substituents in the isoflavone and the structure of the amino alcohol. NMR studies confirmed the interconversion of tautomeric forms.

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Section: Resultsmentioning

confidence: 99%

Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

et al. 2015

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“…Inspection of the reaction conditions already reported by Woodgate et al (1999) indicates that compound II was obtained by reaction of phenylboronic acid and the corresponding tertiary amine. In turn, the authors reported that compound III was obtained unintentionally when using salicylaldehyde benzylamine and boron compounds (Geng et al, 2011).…”

Section: Figurementioning

confidence: 95%

“…Detail of C-HÁ Á ÁO interactions in the title compound (grey and orange dashed lines denote C2-H2Á Á ÁO1 i and C24-H24Á Á ÁO2 ii interactions, respectively). H atoms not involved in these interactions are omitted for clarity [symmetry codes: Woodgate et al, 1999). Specifically, two members of this selected group are structurally related to the title compound: II (MAWDET; Woodgate et al, 1999) and the recently described compound III (EROJIF; Geng & Wu, 2011) ( Fig.…”

Section: Figurementioning

confidence: 99%

Crystal structure ofcis-1-phenyl-8-(pyridin-2-ylmethyl)dibenzo[1,2-c:2,1-h]-2,14-dioxa-8-aza-1-borabicyclo[4.4.0]deca-3,8-diene

et al. 2017

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The title compound, C26H23BN2O2, was obtained as by product during synthetic attempts of a complexation reaction between the tripodal ligand H2L[N,N-bis(2-hydroxybenzyl)(pyridin-2-yl)methylamine] and manganese(III) acetate in the presence of NaBPh4. The isolatedB-phenyl dioxazaborocine contains an N→B dative bond with acisconformation. In the crystal, C—H...O hydrogen bonds define chains parallel to theb-axis direction. A comparative analysis with other structurally related derivatives is also included, together with a rationalization of the unexpected production of this zwitterionic heterocycle.

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“…Taking all these considerations into account, we bring to light our findings on the bis(2-hydroxybenzyl)methylamine (BOMA) framework, with specific focus on a dimethylated variant, MeBOMA (Scheme a). Related ligands have been investigated since the 1950s, , with an especially large contribution by Woodgate et al In all cases, the authors noted the resilience toward hydrolysis of boronic acids upon coordination with the ligand. We therefore began our investigation of the BOMA framework as a possible route toward quaternized boronic acid derivatives with superior stability toward hydrolysis under aqueous basic conditions typical of SM coupling allowing for selective SM cross-coupling (Scheme b).…”

Section: Introductionmentioning

confidence: 99%

Protection of Boronic Acids Using a Tridentate Aminophenol ONO Ligand for Selective Suzuki–Miyaura Coupling

et al. 2023

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Boronic acid protecting group chemistry powerfully enhances the versatility of Suzuki–Miyaura cross-coupling. Prominent examples include trifluoroborate salts, N-methyliminodiacetic acid (MIDA) boronates, and 1,8-diaminonaphthalene boronamides. In this work, we present a bis(2-hydroxybenzyl)methylamine (BOMA) ligand that forms tridentate complexes with boronic acids much like the MIDA ligand but the deprotection is facilitated by organic acids. The BOMA boronates showed considerable stability in both aqueous base and acid, and a variety of chemoselective reactions were performed on these boronates, including selective Suzuki–Miyaura coupling, palladium-catalyzed borylation, ester hydrolysis, alkylation, lithiation–borylation, and oxidative hydroxydeboronation.

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Synthesis of dioxazaborocines from N-substituted-bis(2-hydroxyaryl)aminomethylamines

Cited by 15 publications

References 14 publications

Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

Crystal structure ofcis-1-phenyl-8-(pyridin-2-ylmethyl)dibenzo[1,2-c:2,1-h]-2,14-dioxa-8-aza-1-borabicyclo[4.4.0]deca-3,8-diene

Protection of Boronic Acids Using a Tridentate Aminophenol ONO Ligand for Selective Suzuki–Miyaura Coupling

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